Seth Meyers and the rise of the Chicago writer-performer

Back in 1999 — a gut-wrenching 14 years ago — a theater just north of Wrigley Field was filled on weekend nights with the nervous laughter of people on dates. "Pick-Ups and Hiccups" (a title with admirable descriptive prowess), was a hugely popular sketch-comedy show that poked fun at the absurdity of the mating ritual, a time-honored way to attract a crowd. The show was the work of a couple of wildly disparate writer-performers.

She was zany and quirky and tough to categorize. Her characters were mostly neurotics. When it came to dating, she was all about the hiccups. He was handsome, wry and smooth. So handsome, wry and smooth, in fact, you had the sense some of the young women in the audience would have preferred to drop their goofy, beer-bellied dates and go for him instead. He was all about the pickups, starting with the aspirations of the young professional women in the audience.

The young Seth Meyers would hang around after the show, charming the pants off a changing array of articulate but giggly 20-somethings.

Meyers had met his professional partner, Jill Benjamin, while they both were working at Boom Chicago, the improbably successful Amsterdam outpost of Chicago-style sketch comedy founded in the early 1990s by three guys from Evanston. By the time Meyers and Benjamin had headed to the Netherlands, Boom Chicago was a proven hit with the Dutch, almost all of whom speak English, to answer the obvious question. It was — and still is — a kind of cultural Chicago consulate that deserves some attention from Choose Chicago, the city's new tourism arm. What other authentic, permanent representative is promoting Chicago comedy anywhere else in Europe?

But back to Meyers. This month, he was named to a very select club that people rarely leave: hosts of late-night TV talk shows on major networks. He'll take over NBC's "Late Night" from Jimmy Fallon next year: it's David Letterman's old slot. This is likely to draw increased U.S. media attention to Boom Chicago, to stir some memories in the heads of those singles who flocked to "Pick-Ups and Hiccups" at the old Live Bait Theater and, given the prominence of Meyers' gig, it's as good a time as any to probe the changing profile of the people who come out of the Chicago comedy scene and make it very big.

But first, here's what hasn't changed. Talent needs other talent to thrive. Despite his period of European exile, Meyers certainly was fortunate enough to be in Chicago during an extraordinarily fertile era of Chicago comedy, a time when Tina Fey and Rachel Dratch of Second City also had their own sketch-comedy show ("Dratch and Fey") and when Amy Poehler was to be seen working at i.O., just a few blocks down Clark Street. This remarkable mid-to-late-1990s Chicago comedic ferment (stretch just a little further back, and you also net Amy Sedaris, Stephen Colbert and Steve Carell), has been underanalyzed and underappreciated to date, but I suspect that soon will change. Its alums now make up much of America's entertainment establishment.

The moment in this town has certain commonalities with the era of the Compass Players, and even with the early days of the Steppenwolf Theatre. "Pick-Ups and Hiccups" may have looked like no more than a collection of gags about dating, which is pretty much what it actually was, but it was being performed at an amazing moment in the history of Chicago comedy. It was a time when there was enough of a confluence of individual capability that performers were able to challenge one another at a crucial moment and thus thrive. True fame and fortune required this group to leave Chicago, of course. It always does. But the real formation and development of their work happened here, right in front of the eyes of those of us fortunate enough to be watching.

Meyers' ascension is also notable in another way: It confirms the rise of the Chicago writer-performer, with the writer part driving the bus.

That's especially the kind of writer-performer who, it feels, could be moonlighting as a presidential speechwriter, or op-ed columnist, or news broadcaster. Even more than Fey in the past few years (Fey's persona retains more of an anti-establishment streak), the genial and smart Meyers has ridden the wave of the collapse of the once-solid boundary between news and entertainment. As hitherto stolid news organizations have become interested in show business, and as late-night talk shows have become more driven by current events rather than performances, the camera-ready, poly-hyphenate likes of Meyers have become ever more attractive.

Back in the day, stars emerging from the Chicago scene were more likely to be sweaty characters like John Belushi, Gilda Radner, George Wendt or Chris Farley, or iconoclasts like Alan Arkin or Bill Murray. One did not readily picture any of these figures delivering jokes to White House correspondents or wearing suits. Neither did the decision-makers in the media business. None of these earlier stars were really known as writers, even though write they all did. Chicago's calling card was the instinctive, excessive, no-holds-barred, innately talented physical comedian: a risk-taker and creature of a thousand characters. These were performers rather than personas. You could not imagine those old-school stars interviewing anybody else on a couch, after delivering a wry, up-to-the-minute monologue on Barack Obama's relationship with Congress.

On a more modest level, perhaps, the Radner-Belushi-Murray axis was also in the wheelhouse of Benjamin, Meyers' hugely gifted partner of 14 years ago. As Meyers readily admits, Benjamin's remarkable characters were what made "Pick-Ups and Hiccups" such a great show. All Meyers had to do was play himself: His was the essential, normative persona, the Hugh Grant to Benjamin's Tori Spelling (a comparison they made themselves back then). Meyers mostly had to tee up Benjamin and watch her hit the ball, hilariously, into the rough.

But even on that night 14 years ago, I distinctly remember thinking that Meyers, a wry creature of the fairway, was on his way to fame and fortune and that nobody would ever quite know what to do with Benjamin, who now is a Los Angeles-based actress and improviser with several TV shows to her credit, including the Disney Channel's "Austin & Ally," and a one-woman comedy show, "Jill Benjamin Is Stuck in the 1980s."